CN107205391A - 组蛋白脱甲基酶抑制剂 - Google Patents
组蛋白脱甲基酶抑制剂 Download PDFInfo
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- CN107205391A CN107205391A CN201580061425.6A CN201580061425A CN107205391A CN 107205391 A CN107205391 A CN 107205391A CN 201580061425 A CN201580061425 A CN 201580061425A CN 107205391 A CN107205391 A CN 107205391A
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- CN
- China
- Prior art keywords
- pyrido
- compound
- pharmaceutically acceptable
- pyrimidin
- acceptable salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 108010074870 Histone Demethylases Proteins 0.000 title claims abstract description 40
- 102000008157 Histone Demethylases Human genes 0.000 title claims abstract description 40
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 457
- 238000000034 method Methods 0.000 claims abstract description 125
- -1 pyrido[3,4-d]pyrimidin-4-one derivative compounds Chemical class 0.000 claims abstract description 80
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 30
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 21
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims description 294
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000000623 heterocyclic group Chemical group 0.000 claims description 66
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- AYNNEVPMDRKQCJ-UHFFFAOYSA-N 2-(1-benzylindazol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O AYNNEVPMDRKQCJ-UHFFFAOYSA-N 0.000 claims description 3
- WCSLCBLWILXJIQ-UHFFFAOYSA-N 2-(1-benzylindazol-6-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=CC2=CC=C(C=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O WCSLCBLWILXJIQ-UHFFFAOYSA-N 0.000 claims description 3
- BDGGCQQCOJPBLY-UHFFFAOYSA-N 2-(1-benzylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O BDGGCQQCOJPBLY-UHFFFAOYSA-N 0.000 claims description 3
- GCMRGFKARWMSAN-UHFFFAOYSA-N 2-(1-benzylindol-6-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O GCMRGFKARWMSAN-UHFFFAOYSA-N 0.000 claims description 3
- XYMCOONDOSQQME-UHFFFAOYSA-N 2-(1-cyclopentylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CCCC1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O XYMCOONDOSQQME-UHFFFAOYSA-N 0.000 claims description 3
- OGJOQXKCDODHAH-UHFFFAOYSA-N 2-(1-methylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O OGJOQXKCDODHAH-UHFFFAOYSA-N 0.000 claims description 3
- IJEJFRMSEYJKCB-UHFFFAOYSA-N 2-(2-benzylindazol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=C2C=CC(=CC2=C1)OC=1N=C(C2=C(N=1)C=NC=C2)O IJEJFRMSEYJKCB-UHFFFAOYSA-N 0.000 claims description 3
- BBDTWEHTHUQEHL-UHFFFAOYSA-N 2-(2-benzylindazol-6-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N1N=C2C=C(C=CC2=C1)OC=1N=C(C2=C(N=1)C=NC=C2)O BBDTWEHTHUQEHL-UHFFFAOYSA-N 0.000 claims description 3
- UQBJLMBNRBGNMX-UHFFFAOYSA-N 2-[(1-phenyl-2,3-dihydroindol-5-yl)oxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)N1CCC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O UQBJLMBNRBGNMX-UHFFFAOYSA-N 0.000 claims description 3
- UOHPJYFCEUANGX-UHFFFAOYSA-N 2-[(1-phenyl-3,4-dihydro-2H-quinolin-6-yl)oxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)N1CCCC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O UOHPJYFCEUANGX-UHFFFAOYSA-N 0.000 claims description 3
- SEIZYXWRENFQFK-UHFFFAOYSA-N 2-[1-(1-phenylethyl)indol-5-yl]oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C(C)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O SEIZYXWRENFQFK-UHFFFAOYSA-N 0.000 claims description 3
- YDTRYKRNDCZZPP-UHFFFAOYSA-N 2-[3-(N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C=1C=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=CC=1)C1=CC=CC=C1 YDTRYKRNDCZZPP-UHFFFAOYSA-N 0.000 claims description 3
- ILUHNCDZOBKFNT-UHFFFAOYSA-N 2-[3-[benzyl(methyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C=1C=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=CC=1)C ILUHNCDZOBKFNT-UHFFFAOYSA-N 0.000 claims description 3
- YKNIDCVIHXRDHC-UHFFFAOYSA-N 2-[3-fluoro-4-(N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound FC=1C=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=CC=1N(C1=CC=CC=C1)C YKNIDCVIHXRDHC-UHFFFAOYSA-N 0.000 claims description 3
- XIBIGJJNITZXIB-UHFFFAOYSA-N 2-[4-(2-phenylmorpholin-4-yl)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C1CN(CCO1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 XIBIGJJNITZXIB-UHFFFAOYSA-N 0.000 claims description 3
- COBYQVQJCZYEBC-UHFFFAOYSA-N 2-[4-(3-methoxy-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COC=1C=C(C=CC=1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C COBYQVQJCZYEBC-UHFFFAOYSA-N 0.000 claims description 3
- KSZDGLQJEJYGMA-UHFFFAOYSA-N 2-[4-(3-phenylpiperidin-1-yl)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C1CN(CCC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 KSZDGLQJEJYGMA-UHFFFAOYSA-N 0.000 claims description 3
- NCRVLFZFQTZIPS-UHFFFAOYSA-N 2-[4-(4-cyclopropyl-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CC1)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C NCRVLFZFQTZIPS-UHFFFAOYSA-N 0.000 claims description 3
- RQZSATFWCBCUIO-UHFFFAOYSA-N 2-[4-(4-methoxy-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C RQZSATFWCBCUIO-UHFFFAOYSA-N 0.000 claims description 3
- AFHPEJCZXXGCJW-UHFFFAOYSA-N 2-[4-(N,3-dimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C=1C=C(C=CC=1)C AFHPEJCZXXGCJW-UHFFFAOYSA-N 0.000 claims description 3
- MSRPQWORNNWNAO-UHFFFAOYSA-N 2-[4-(N,4-dimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=C(C=C1)C MSRPQWORNNWNAO-UHFFFAOYSA-N 0.000 claims description 3
- FXOZDODFBPBHLG-UHFFFAOYSA-N 2-[4-(N-ethyl-4-propan-2-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=C(C=C1)C(C)C FXOZDODFBPBHLG-UHFFFAOYSA-N 0.000 claims description 3
- WBUXXLSZHBPOSW-UHFFFAOYSA-N 2-[4-(N-methyl-3-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC(=CC=C1)N1CCOCC1 WBUXXLSZHBPOSW-UHFFFAOYSA-N 0.000 claims description 3
- WLMRSZUYFSTETI-UHFFFAOYSA-N 2-[4-(N-methyl-4-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=C(C=C1)N1CCOCC1 WLMRSZUYFSTETI-UHFFFAOYSA-N 0.000 claims description 3
- YELYEKBMSXCDGL-UHFFFAOYSA-N 2-[4-(N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC=CC=C1 YELYEKBMSXCDGL-UHFFFAOYSA-N 0.000 claims description 3
- IDWQEMVQZNXZTI-UHFFFAOYSA-N 2-[4-[4-(1-cyclopropylethyl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(CC1)C(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C IDWQEMVQZNXZTI-UHFFFAOYSA-N 0.000 claims description 3
- BPAPEWQJFYHACY-UHFFFAOYSA-N 2-[4-[4-(1-methoxyethyl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C BPAPEWQJFYHACY-UHFFFAOYSA-N 0.000 claims description 3
- RCKIYJJKTLSRJU-UHFFFAOYSA-N 2-[4-[4-(1-methoxypropan-2-yl)-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C RCKIYJJKTLSRJU-UHFFFAOYSA-N 0.000 claims description 3
- DALZREFYBLXCFJ-UHFFFAOYSA-N 2-[4-[4-[1-[2-methoxyethyl(methyl)amino]propan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound COCCN(CC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C)C DALZREFYBLXCFJ-UHFFFAOYSA-N 0.000 claims description 3
- VAYGMXWSYWYQSI-UHFFFAOYSA-N 2-[4-[4-[4-(dimethylamino)butan-2-yl]-N-methylanilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(CCC(C)C1=CC=C(C=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C)C VAYGMXWSYWYQSI-UHFFFAOYSA-N 0.000 claims description 3
- NVRHIDHPBHNKJX-UHFFFAOYSA-N 2-[4-[N-methyl-3-(4-methylpiperazin-1-yl)anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC(=CC=C1)N1CCN(CC1)C NVRHIDHPBHNKJX-UHFFFAOYSA-N 0.000 claims description 3
- HIEXVOBPEWWGJY-UHFFFAOYSA-N 2-[4-[N-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=CC(=CC=C1)CN1CCN(CC1)C HIEXVOBPEWWGJY-UHFFFAOYSA-N 0.000 claims description 3
- CNQMUOQMQVAVEI-UHFFFAOYSA-N 2-[4-[benzyl(methyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C CNQMUOQMQVAVEI-UHFFFAOYSA-N 0.000 claims description 3
- VXWMVXOIQLLKMN-UHFFFAOYSA-N 2-[4-[methyl(2-phenylethyl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)CCC1=CC=CC=C1 VXWMVXOIQLLKMN-UHFFFAOYSA-N 0.000 claims description 3
- VKDUSQPGXRXKMN-UHFFFAOYSA-N 2-[4-[methyl(pyridin-2-yl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C1=NC=CC=C1 VKDUSQPGXRXKMN-UHFFFAOYSA-N 0.000 claims description 3
- XKBXFTPKURQNCU-UHFFFAOYSA-N 2-[4-[methyl-(5-propan-2-ylpyridin-2-yl)amino]phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)C=1C=CC(=NC=1)N(C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1)C XKBXFTPKURQNCU-UHFFFAOYSA-N 0.000 claims description 3
- BWUXABKTZMTAQE-UHFFFAOYSA-N 3-[N-methyl-4-[(4-oxo-3H-pyrido[3,4-d]pyrimidin-2-yl)oxy]anilino]benzonitrile Chemical compound OC=1C2=C(N=C(N=1)OC1=CC=C(C=C1)N(C=1C=C(C#N)C=CC=1)C)C=NC=C2 BWUXABKTZMTAQE-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- VEMHOQINGBWINF-UHFFFAOYSA-N N-methyl-N-[4-[(4-oxo-3H-pyrido[3,4-d]pyrimidin-2-yl)oxy]phenyl]-2-phenylacetamide Chemical compound OC=1C2=C(N=C(N=1)OC1=CC=C(C=C1)N(C(CC1=CC=CC=C1)=O)C)C=NC=C2 VEMHOQINGBWINF-UHFFFAOYSA-N 0.000 claims description 3
- DOBZVGBVNPHCFT-UHFFFAOYSA-N 2-(1-phenylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O DOBZVGBVNPHCFT-UHFFFAOYSA-N 0.000 claims description 2
- AVPBNCDXCUBCFD-UHFFFAOYSA-N 2-(1-piperidin-4-ylindol-5-yl)oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1CCC(CC1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O AVPBNCDXCUBCFD-UHFFFAOYSA-N 0.000 claims description 2
- LPQYVJZVLPGAOE-UHFFFAOYSA-N 2-[1-(oxan-4-yl)indol-5-yl]oxy-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound O1CCC(CC1)N1C=CC2=CC(=CC=C12)OC=1N=C(C2=C(N=1)C=NC=C2)O LPQYVJZVLPGAOE-UHFFFAOYSA-N 0.000 claims description 2
- GGHUFCYASQYURN-UHFFFAOYSA-N 2-[4-(2-fluoro-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC=C(OC2=NC3=CN=CC=C3C(O)=N2)C=C1)C1=CC=CC=C1F GGHUFCYASQYURN-UHFFFAOYSA-N 0.000 claims description 2
- WPXNVAPMYMQGFE-UHFFFAOYSA-N 2-[4-(3-chloro-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound ClC=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1 WPXNVAPMYMQGFE-UHFFFAOYSA-N 0.000 claims description 2
- KPJXVEMQMLXZMH-UHFFFAOYSA-N 2-[4-(3-fluoro-N,4-dimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound FC=1C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=CC=1C KPJXVEMQMLXZMH-UHFFFAOYSA-N 0.000 claims description 2
- GVRPQGJEOVBHLR-UHFFFAOYSA-N 2-[4-(3-phenylpyrrolidin-1-yl)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C1CN(CC1)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 GVRPQGJEOVBHLR-UHFFFAOYSA-N 0.000 claims description 2
- GLOALBZJXBQZTJ-UHFFFAOYSA-N 2-[4-(4-chloro-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 GLOALBZJXBQZTJ-UHFFFAOYSA-N 0.000 claims description 2
- QMWFMZMUWRTMPB-UHFFFAOYSA-N 2-[4-(4-ethyl-N-methyl-3-morpholin-4-ylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)C1=C(C=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1)N1CCOCC1 QMWFMZMUWRTMPB-UHFFFAOYSA-N 0.000 claims description 2
- JXJFONPGIZCSTF-UHFFFAOYSA-N 2-[4-(4-ethyl-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 JXJFONPGIZCSTF-UHFFFAOYSA-N 0.000 claims description 2
- CHULWJUZMOFOBC-UHFFFAOYSA-N 2-[4-(4-tert-butyl-N-methylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)(C)C1=CC=C(N(C)C2=CC=C(OC=3N=C(C4=C(N=3)C=NC=C4)O)C=C2)C=C1 CHULWJUZMOFOBC-UHFFFAOYSA-N 0.000 claims description 2
- LEEOBDATXTXUKR-UHFFFAOYSA-N 2-[4-(N,3,4-trimethylanilino)phenoxy]-3H-pyrido[3,4-d]pyrimidin-4-one Chemical compound CN(C1=CC(=C(C=C1)C)C)C1=CC=C(OC=2N=C(C3=C(N=2)C=NC=C3)O)C=C1 LEEOBDATXTXUKR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 235000019187 sodium-L-ascorbate Nutrition 0.000 description 1
- 239000011755 sodium-L-ascorbate Substances 0.000 description 1
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MCNMZLIJAOGTJQ-UHFFFAOYSA-N tert-butyl n-(5-bromopyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CN=CC(Br)=C1 MCNMZLIJAOGTJQ-UHFFFAOYSA-N 0.000 description 1
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
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- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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- 239000003039 volatile agent Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US201462051691P | 2014-09-17 | 2014-09-17 | |
| US62/051,691 | 2014-09-17 | ||
| PCT/US2015/050432 WO2016044429A1 (en) | 2014-09-17 | 2015-09-16 | Histone demethylase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107205391A true CN107205391A (zh) | 2017-09-26 |
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| CN201580061425.6A Pending CN107205391A (zh) | 2014-09-17 | 2015-09-16 | 组蛋白脱甲基酶抑制剂 |
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| EP (2) | EP3193601B1 (enExample) |
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| KR (1) | KR20170048591A (enExample) |
| CN (1) | CN107205391A (enExample) |
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| BR (1) | BR112017005511A2 (enExample) |
| CA (1) | CA2961610A1 (enExample) |
| CL (1) | CL2017000659A1 (enExample) |
| CO (1) | CO2017003538A2 (enExample) |
| EA (1) | EA201790603A1 (enExample) |
| EC (1) | ECSP17023551A (enExample) |
| ES (1) | ES2910226T3 (enExample) |
| IL (1) | IL251179A0 (enExample) |
| MX (1) | MX2017003466A (enExample) |
| SG (1) | SG11201702147TA (enExample) |
| WO (1) | WO2016044429A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115368252A (zh) * | 2022-09-19 | 2022-11-22 | 西北农林科技大学 | 一种4-胺基酚类衍生物及应用 |
| CN116253712A (zh) * | 2023-03-27 | 2023-06-13 | 昆山市第一人民医院 | 5,6,7-三甲氧基-2,3-二氢喹啉类化合物、药物组合物及用途 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS56561B1 (sr) | 2013-03-15 | 2018-02-28 | Quanticel Pharmaceuticals Inc | Inhibitori histon demetilaze |
| KR20170048591A (ko) | 2014-09-17 | 2017-05-08 | 셀젠 콴티셀 리서치, 인크. | 히스톤 데메틸라제 억제제 |
| JP6970681B2 (ja) * | 2016-03-15 | 2021-11-24 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
| US10150754B2 (en) | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| MY199852A (en) | 2016-11-28 | 2023-11-25 | Teijin Pharma Ltd | Crystal of pyrido[3,4-d]pyrimidine derivative or solvate thereof |
| US11040973B2 (en) | 2017-03-29 | 2021-06-22 | Purdue Research Foundation | Inhibitors of kinase networks and uses thereof |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070190634A1 (en) * | 2002-03-15 | 2007-08-16 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| US20070254901A1 (en) * | 2004-08-23 | 2007-11-01 | Bilodeau Mark T | Inhibitors of Akt Activity |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003033472A1 (en) * | 2001-10-17 | 2003-04-24 | Kirin Beer Kabushiki Kaisha | Quinoline or quinazoline derivatives inhibiting auto- phosphorylation of fibroblast growth factor receptors |
| JP2007501854A (ja) * | 2003-05-27 | 2007-02-01 | ファイザー・プロダクツ・インク | 受容体型チロシンキナーゼ阻害薬としてのキナゾリン類およびピリド［３，４−ｄ］ピリミジン類 |
| FR2876103B1 (fr) | 2004-10-01 | 2008-02-22 | Aventis Pharma Sa | Nouveaux derives bis-azaindoles, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| CA2662937A1 (en) | 2006-09-11 | 2008-03-20 | Curis, Inc. | Multi-functional small molecules as anti-proliferative agents |
| TW200922590A (en) | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
| JP5552608B2 (ja) | 2012-04-27 | 2014-07-16 | 株式会社ソフイア | 遊技機 |
| CN104981458B (zh) | 2012-10-02 | 2017-07-21 | 吉利德科学公司 | 组蛋白去甲基化酶抑制剂 |
| HUE037312T2 (hu) | 2012-12-19 | 2018-08-28 | Celgene Quanticel Res Inc | Hiszton demetiláz inhibitorok |
| KR20150100814A (ko) | 2012-12-21 | 2015-09-02 | 콴티셀 파마슈티컬스, 인크. | 히스톤 데메틸라제 억제제 |
| EP2968282B1 (en) | 2013-03-12 | 2018-05-09 | Celgene Quanticel Research, Inc. | Histone dementhylase inhibitors |
| RS56561B1 (sr) | 2013-03-15 | 2018-02-28 | Quanticel Pharmaceuticals Inc | Inhibitori histon demetilaze |
| CN105339001A (zh) | 2013-03-15 | 2016-02-17 | 基因泰克公司 | 治疗癌症和预防癌症耐药性的方法 |
| NZ728120A (en) | 2014-06-25 | 2023-06-30 | Celgene Quanticel Res Inc | Histone demethylase inhibitors |
| KR20170048591A (ko) | 2014-09-17 | 2017-05-08 | 셀젠 콴티셀 리서치, 인크. | 히스톤 데메틸라제 억제제 |
| US10030017B2 (en) | 2014-09-17 | 2018-07-24 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| JP6970681B2 (ja) | 2016-03-15 | 2021-11-24 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
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2015
- 2015-09-16 KR KR1020177009917A patent/KR20170048591A/ko not_active Withdrawn
- 2015-09-16 CA CA2961610A patent/CA2961610A1/en not_active Abandoned
- 2015-09-16 EA EA201790603A patent/EA201790603A1/ru unknown
- 2015-09-16 WO PCT/US2015/050432 patent/WO2016044429A1/en not_active Ceased
- 2015-09-16 SG SG11201702147TA patent/SG11201702147TA/en unknown
- 2015-09-16 CN CN201580061425.6A patent/CN107205391A/zh active Pending
- 2015-09-16 EP EP15842574.4A patent/EP3193601B1/en not_active Not-in-force
- 2015-09-16 ES ES15842574T patent/ES2910226T3/es active Active
- 2015-09-16 US US14/855,950 patent/US9643965B2/en active Active
- 2015-09-16 MX MX2017003466A patent/MX2017003466A/es unknown
- 2015-09-16 EP EP18181949.1A patent/EP3453710B1/en active Active
- 2015-09-16 JP JP2017514615A patent/JP6552608B2/ja not_active Expired - Fee Related
- 2015-09-16 AU AU2015317806A patent/AU2015317806A1/en not_active Abandoned
- 2015-09-16 BR BR112017005511A patent/BR112017005511A2/pt not_active Application Discontinuation
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2017
- 2017-03-15 IL IL251179A patent/IL251179A0/en unknown
- 2017-03-17 CL CL2017000659A patent/CL2017000659A1/es unknown
- 2017-04-12 CO CONC2017/0003538A patent/CO2017003538A2/es unknown
- 2017-04-17 EC ECIEPI201723551A patent/ECSP17023551A/es unknown
- 2017-05-05 US US15/588,561 patent/US10112940B2/en active Active
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2018
- 2018-09-20 US US16/137,219 patent/US10611763B2/en active Active
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2020
- 2020-02-14 US US16/790,878 patent/US10815234B2/en active Active
- 2020-09-21 US US17/026,763 patent/US11535616B2/en active Active
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2022
- 2022-11-03 US US17/980,291 patent/US12172998B2/en active Active
-
2024
- 2024-11-01 US US18/935,237 patent/US20250066355A1/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070190634A1 (en) * | 2002-03-15 | 2007-08-16 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| US20070254901A1 (en) * | 2004-08-23 | 2007-11-01 | Bilodeau Mark T | Inhibitors of Akt Activity |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115368252A (zh) * | 2022-09-19 | 2022-11-22 | 西北农林科技大学 | 一种4-胺基酚类衍生物及应用 |
| CN115368252B (zh) * | 2022-09-19 | 2024-01-12 | 西北农林科技大学 | 一种4-胺基酚类衍生物及应用 |
| CN116253712A (zh) * | 2023-03-27 | 2023-06-13 | 昆山市第一人民医院 | 5,6,7-三甲氧基-2,3-二氢喹啉类化合物、药物组合物及用途 |
| CN116253712B (zh) * | 2023-03-27 | 2025-05-02 | 昆山市第一人民医院 | 5,6,7-三甲氧基-2,3-二氢喹啉类化合物、药物组合物及用途 |
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